N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide

Base Information

• Chemical Name: N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide
• CAS No.: 180344-13-2
• Molecular Formula: C₃₇H₅₄Cl₃N₅O₇S
• Molecular Weight: 819.29

Synonyms:N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide

Chemical Property of N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide

Chemical Property:

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Technology Process of N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide

There total 9 articles about N¹-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N⁴-<2-(dimethylamino)-2-oxoethyl>-N⁴-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 32.0%

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (122621-77-6) + N-dimethylcarbamoylmethyl-N-(1-phenyl-ethyl)-2-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-ylmethyl]-succinamic acid (160938-17-0) → N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-(dimethylamino)-2-oxoethyl>-N4-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide (180344-13-2)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25 ℃; for 3.5h;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

N,N-dimethyl-2-<<1(S)-phenylethyl>amino>acetamide (160937-99-5) → N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-(dimethylamino)-2-oxoethyl>-N4-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide (180344-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 h / 25 °C

2: 30 percent H₂O₂, LiOH*H₂O / H₂O; trifluoroacetic acid / 1.) 0 deg C, 1.5 h, 2.) 25 deg C, 3.5 h

3: 32 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 3.5 h / 25 °C

With lithium hydroxide; dihydrogen peroxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/S0968-0896(98)00265-X

Reference yield:

3-(5-bromo-1,4-dioxopentyl)-4(S)-(1-methylethyl)-2-oxazolidinone (160447-17-6) → N1-<1(S)-(cyclohexylmethyl)-2(R),3(S)-dihydroxy-5-methylhexyl>-N4-<2-(dimethylamino)-2-oxoethyl>-N4-<1(S)-phenylethyl>-2(R)-<<(2,2,2-trichloroethoxy)carbonyl>amino>-4-thiazolylmethylbutanediamide (180344-13-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 55 percent / tetrahydrofuran / 25 °C

2: 4.23 g / thiourea / propan-2-ol / 0.5 h / Heating

3: 61 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 1.) 0 deg C, 45 min, 2.) 25 deg C, 16 h

4: 59 percent / NaHMDS / tetrahydrofuran / -78 °C / 1.) 45 min, 2.) 2 h

5: TFA / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 25 deg C, 3 h

6: 73 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 25 h / 25 °C

7: 30 percent H₂O₂, LiOH*H₂O / H₂O; trifluoroacetic acid / 1.) 0 deg C, 1.5 h, 2.) 25 deg C, 3.5 h

8: 32 percent / i-Pr₂NEt, BOP*PF₆ / dimethylformamide / 3.5 h / 25 °C

With dmap; lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; thiourea; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; trifluoroacetic acid;

DOI:10.1016/S0968-0896(98)00265-X

upstream raw materials:

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

N-dimethylcarbamoylmethyl-N-(1-phenyl-ethyl)-2-[2-(2,2,2-trichloro-ethoxycarbonylamino)-thiazol-4-ylmethyl]-succinamic acid

N,N-dimethyl-2-<<1(S)-phenylethyl>amino>acetamide

3-(5-bromo-1,4-dioxopentyl)-4(S)-(1-methylethyl)-2-oxazolidinone

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